When New York Mayor Michael Bloomberg tapped Cathie Black to be schools chancellor, a lowly intern filed a freedom of information request that the city fought for two years. Now, that intern reflects on why the mayor tried so hard to keep secret emails that turned out to be innocuous

In November 2010, I was earning $300 a week for The Village Voice, blogging about unemployed actors who moonlit as bed bug exterminators and a city project to make biofuel out of toilet water. One afternoon, then-Schools Chancellor Joel Klein stunned the city by suddenly resigning his post of eight years for a job at Rupert Murdoch's News Corporation.

The bigger shock that day was who New York City Mayor Michael Bloomberg chose as Klein's successor: Cathie Black, the Hearst Magazines chairwoman who, as far as anybody could tell, had never stepped foot in a public school, let alone knew how to run one (or the city's 1,700, for that matter).

So I fired off a routine Freedom of Information request to the mayor's office, seeking emails between Black, Bloomberg and their staffs.

When the emails were finally released last week, after a two-year legal battle, they revealed a desperate public relations campaign in which city officials tried to rally support from prominent women — including Oprah Winfrey, Gloria Steinem, Caroline Kennedy, and Bette Midler — to champion Black's appointment. (I will admit: never in a million years did I expect my work to result in stories containing the sentence, "Ms. Winfrey couldn't be reached for comment.") In the end, the emails were amusing, slightly enlightening, but largely innocuous.

Which is why it's so puzzling that the city fought all the way to the state's highest court to block their release. Cathie Black resigned as schools chancellor after just 95 days on the job. The case to keep her emails secret would last more than six times as long.

If I hadn't had high-powered help, the city would surely have won, and quickly. The city initially denied my request and, after I had exhausted an administrative appeals process, John Cook — now the editor of Gawker — put me in touch with a media law clinic at Yale Law School.

The Bulldogs and Elizabeth Wolstein — a partner at Schlam, Stone & Dolan who once supervised appeals for the U.S. Attorney in the U.S. Court of Appeals for the Second Circuit — agreed to take the case, pro bono, propelling a fresh-out-of-NYU, semi-employed, then-21-year-old journalist into a courtroom battle with New York's billionaire, third-term mayor.

We filed our lawsuit in May 2011 andwon a judgment from the state's Supreme Court — New York's trial court — that Thanksgiving. The city appealed, drawing the process out another two years.

Last Halloween, Paulson showed up to the courthouse on East 25th Street and Madison Avenue. The five-judge panels in this courthouse hear appeals for civil and criminal cases in Manhattan and the Bronx, and at 3:10 that afternoon, Paulson took to the lectern and presented the city's argument.

While Black was not yet on the government's payroll when the emails in question were written, she was nonetheless acting as a "consultant" to the mayor, Paulson said, because she was acting at his direction to further one of his policy goals. What was that goal? Securing Black's own position on the government's payroll.

In her original order, trial court Judge Alice Schlesinger had minced no words, calling this argument "particularly specious" and "wholly devoid of merit." The five judges on the appellate panel also rejected the city's claim.

But the city persisted and tried to get a hearing in the state's highest court, the Court of Appeals, claiming the case now represented a novel and statewide issue.

I'd often been asked why I thought the city was fighting so doggedly to keep these emails secret. But without having seen them, it was difficult to say whether there was a sinister motive or a more legitimate reason.

While petitioning the Court of Appeals to take the case, the city began to make its policy concerns clearer. Disclosing communications with people who were appointed to, but had not yet taken, office would make it more difficult to lure good talent from the private sector, it argued. Of course, people considering public service know they are stepping under a public microscope.

There is also an interest, the argument goes, in allowing government officials some degree of privacy to do their work, so they can deliberate freely and candidly. That is the reason certain communications within and between government agencies are often exempt from disclosure under public transparency laws. These days, of course, much of that deliberation occurs electronically, creating a permanent record. Ardent transparency advocates often want those records open, too, arguing we shouldn't have any smoke-filled rooms — literal or virtual.

"The City believes that the principles permitting government employees to exchange opinions, advice and criticism freely and frankly, without the chilling prospect of public disclosure, should extend to individuals who have been elected or selected to public office but have not yet assumed office," Paulson wrote me — in an email, of course — answering a question for this article.

The question is where, exactly, to draw the line? Suppose the public backlash had forced Bloomberg to abandon hiring Black as chancellor, or that Black herself had withdrawn from the running. Could the emails have been kept secret merely because she had, at one point, been considered for the job? What, then, would prohibit an agency from withholding records of true public import by simply claiming that the Mayor was thinking about hiring John Doe to be his next Deputy Junior Assistant Something-or-Other someday?

While the city maintains it fought for the principle of free and candid communications, there's another theory as to why the mayor's office resisted disclosing these emails: It feared a precedent that would open the floodgates to release other ones that might be worse than embarrassing.